The Intramolecular Aromatic Electrophilic Substitution of Aminocyclopropanes Prepared by the Kulinkovich-de Meijere Reaction

This article describes new examples of intramolecular Kulinkovich–de Meijere reactions applied to carboxylic amides bearing an olefin moiety and an aromatic ring at a suitable position. Upon heating, the aminocyclopropanes thus obtained undergo intramolecular aromatic electrophilic substitution to a...

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Veröffentlicht in:	European Journal of Organic Chemistry 2005-11, Vol.2005 (21), p.4654-4662
Hauptverfasser:	Larquetoux, Laurent, Ouhamou, Nouara, Chiaroni, Angèle, Six, Yvan
Format:	Artikel
Sprache:	eng
Schlagworte:	Amides Aromatic substitution Chemical Sciences Cyclisation Cyclopropanes Organic chemistry Titanium
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container_end_page	4662
container_issue	21
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container_title	European Journal of Organic Chemistry
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creator	Larquetoux, Laurent Ouhamou, Nouara Chiaroni, Angèle Six, Yvan
description	This article describes new examples of intramolecular Kulinkovich–de Meijere reactions applied to carboxylic amides bearing an olefin moiety and an aromatic ring at a suitable position. Upon heating, the aminocyclopropanes thus obtained undergo intramolecular aromatic electrophilic substitution to afford polycyclic systems. Among the various starting materials prepared, best results are obtained from indole and phenol derivatives. In each case, a benzylic quaternary centre is introduced at the newly‐formed ring junction. On one example, the efficiency of the cyclisation has been dramatically improved using a catalytic amount of para‐toluenesulfonic acid. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
doi_str_mv	10.1002/ejoc.200500428
format	Article
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subjects	Amides Aromatic substitution Chemical Sciences Cyclisation Cyclopropanes Organic chemistry Titanium
title	The Intramolecular Aromatic Electrophilic Substitution of Aminocyclopropanes Prepared by the Kulinkovich-de Meijere Reaction
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